(IUCr) 2-Methyl-5-(4-tolyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

Volume 64
Part 1
Page o212
January 2008

Received 14 November 2007
Accepted 29 November 2007
Online 6 December 2007

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.057
wR = 0.227
Data-to-parameter ratio = 19.8
Details

2-Methyl-5-(4-tolyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

Clarissa P. Frizzo,^a Patrick T. Campos,^a Mara R. B. Marzari,^a Pablo Machado ^a and Marcos A. P. Martins ^a ^*

^aNúcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, RS, Brazil
Correspondence e-mail: mmartins@base.ufsm.br

In the title compound, C₁₅H₁₂F₃N₃, the pyrazolo[1,5-a]pyrimidine system ring is essentially planar with a maximum deviation from the mean plane of 0.014 (1) Å. The 4-tolyl group makes a dihedral angle of 14.1 (1)° with the pyrazolo[1,5-a]pyrimidine ring system. The crystal packing is stabilized mainly by van der Waals forces.

Related literature

For related pyrazolopyrimidine compounds, see: Wen et al. (2004, 2005); Oliveira-Campos et al. (2006). For related literature and the synthetic procedure, see: Martins et al. (2004, 2006). For the pharmacological activity, see: Almanza et al. (2001); Novinson et al. (1977); George (2001).

Experimental

Crystal data

C₁₅H₁₂F₃N₃
M_r = 291.28
Triclinic, $[P \overline 1]$
a = 4.8715 (2) Å
b = 11.2655 (5) Å
c = 13.5584 (6) Å
= 110.225 (3)°
= 96.808 (3)°
= 99.835 (3)°
V = 675.13 (5) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 293 (2) K
0.98 × 0.21 × 0.20 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (XPREP; Bruker, 2006) T_min = 0.874, T_max = 0.977
16787 measured reflections
3757 independent reflections
2200 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.227
S = 1.05
3757 reflections
190 parameters
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.45 e Å^-3

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2373 ).

Acknowledgements

The authors thank the Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq/PRONEX) and Fundação de Amparo à Pesquisa do Estado do Rio Grande do Sul (FAPERGS) for financial support. The fellowships from CNPq and CAPES are also acknowledged. The diffractometer was funded by a CT-INFRA grant from the Financiadora de Estudos e Projetos (FINEP), Brazil.

References

Almanza, C., Arriba, F. A., Cavalcanti, F. L., Gómez, L. A., Miralle, A., Merlos, M., Rafanell, J. G. & Forn, J. (2001). J. Med. Chem. 44, 350-361.
Bruker (2006). APEX2 (Version 2.1), SAINT (Version 7.34A) and XPREP (Version 2005/4). Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
George, C. F. P. (2001). Lancet, 358, 1623-1626.
Martins, M. A. P., Cunico, W., Pereira, C. M. P., Sinhorin, A. P., Flores, A. F. C., Bonacorso, H. G. & Zanatta, N. (2004). Curr. Org. Synth. 1, 391-403 and references therein.
Martins, M. A. P., Cunico, W., Scapin, E., Emmerich, D. J., Fiss, G. F., Rosa, F. A., Bonacorso, H. B., Zanatta, N. & Flores, A. F. C. (2006). Lett. Org. Chem. 3, 358-362.
Novinson, T., Robins, R. K. & Matthews, T. R. (1977). J. Med. Chem. 20, 296-299.
Oliveira-Campos, A. M. F., Rodrigues, L. M., Kaja, M., Guilardi, S., Franca, E. de F. & Ellena, J. (2006). Acta Cryst. E62, o5246-o5248.
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany.
Wen, L.-R., Wang, S.-W., Li, M. & Guo, W.-S. (2005). Acta Cryst. E61, o1459-o1460.
Wen, L.-R., Wang, S.-W., Xu, H.-Z., Zhang, X.-L., Li, M. & Liu, J.-H. (2004). Acta Cryst. E60, o1294-o1295.

organic compounds